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Why Software Projects Miss Deadlines: The Known and the Unknown

By In Technology

Software development deadlines. They haunt our dreams, ruin our weekends, and yet, somehow, we’re always shocked when we miss them. From tiny web projects to colossal AAA games, the software industry has an infamously bad reputation for blowing past deadlines and budgets. But how do software engineers manage to be worse than, say, the folks who bid on highway systems?

The Known Unknowns: We Sort of Know What We’re Dealing With

Before we tackle the real villain, let’s touch on the “known unknowns.” These are the things we anticipate will pose questions or challenges. When a project kicks off, developers huddle with domain experts to map out the grand plan. This early phase is rife with questions:

  1. Architectural Trade-offs: “Should we use Framework X for rapid development? Will it scale if our user base explodes?”
  2. Technical Feasibility: “Is there a library that does what we need? Do we have to build it from scratch?”
  3. Project Management Triangle: “Do we write quick-and-dirty code now, knowing we’ll refactor later, or aim for scalability and security from the get-go?”

These questions are predictable and somewhat manageable. We know they’ll pop up and can plan (read: guesstimate) for them. But then come the…

Unknown Unknowns

Unknown unknowns are the sneaky, unpredictable gremlins that can throw a project into chaos. They are the reason even the most detailed plans can blow up spectacularly.

Examples of Unknown Unknowns

So, what do these elusive unknown unknowns look like in practice? Here are a few examples:

  • The Market/Product Changes: This is the most common. When you’re building software you are building it for an end user with a purpose in mind. But you can never know FOR SURE that you’re building the right thing. You will only really know what needs to change when you first watch a user play with it. That’s why it’s so important to get it into the hands of real users as quickly as possible.
  • Emerging Technology Changes: A new version of a critical framework or library is released midway through your project, rendering your current approach obsolete.
  • Unforeseen Integration Issues: An external API you depend on changes or is deprecated without warning, requiring significant rework. This literally happened to me this week, and I spent two days fixing a problem that worked the first time with the old API. And this was a tiny python script and a Make.com workflow… not some giant HIPAA compliant stack that has five engineers working on it. That kind of change could mess up a project by months.
  • Unexpected User Behavior: During testing, users interact with your software in completely unanticipated ways, uncovering bugs and usability issues that require substantial fixes. Think of yourself as an explorer here; learning new ways your system can be used, and how users can f*@&k it up.
  • Regulatory Changes: New laws or industry regulations come into effect, necessitating changes to your software to remain compliant.
  • Team Changes: Key team members leave the project, taking with them critical knowledge and slowing down progress as new members are onboarded.

The Exploratory Nature of Software Development

Software development often feels like your are Indiana Jones navigating a jungle with a half-baked map. Sure, you have a rough idea of where you’re going, but the terrain can change unexpectedly. When developers estimate how long a task will take, they’re picturing a perfect world scenario. It’s tough to convey to managers or clients—who often see programming as a kind of magic—why one feature is a cakewalk and another is a nightmare.

Agile vs. Waterfall: Why Flexibility Matters

This is why traditional waterfall methodologies, which demand every detail be nailed down upfront, often fail in software development. Designing everything on paper without accounting for unforeseen problems is a recipe for disaster. Agile methodologies, with their iterative and flexible nature, help mitigate the chaos of unknown unknowns by allowing for continuous reassessment and adaptation.

Agile is by no means perfect though. Agile projects fail for different reasons: scope creep, running out of budget, not being disciplined in prioritizing features, not launching quick enough, over-engineering, and plain old building bad software.

The Myth of Big Design Up Front

Big design upfront (BDUF) robs software of its most powerful trait: adaptability. The ability to iterate, update, and improve on the fly is crucial. Agile approaches embrace this, understanding that no one can predict every challenge. The flexibility to pivot based on real-world feedback and emerging obstacles is what keeps projects on track—relatively speaking.

Making Software Development More Predictable

While we can’t eliminate all the unknowns, there are strategies to make software development more predictable. The problem is that most of this stuff makes you slow down. There is always a trade off. So enjoy!

  1. LAUCH EARLY AND OFTEN: Get your system into the hands of real users as soon as possible. If you’re not embarrassed to let users play with it, you’ve launched too late. I just wrote about this.
  2. Adopt Agile Methodologies: Agile frameworks like Scrum and Kanban promote iterative development, continuous feedback, and flexibility, making it easier to adapt to changes and unforeseen issues.
  3. Frequent Check-ins and Reviews: Regularly scheduled reviews, stand-ups, and retrospectives help catch issues early, before they spiral out of control.
  4. Automated Testing: Implement a robust suite of automated tests to catch regressions and integration issues early in the development process.
  5. Continuous Integration/Continuous Deployment (CI/CD): Use CI/CD pipelines to automate the deployment process, ensuring that new code integrates smoothly with existing systems.
  6. Risk Management: Proactively identify potential risks and develop contingency plans to address them if they arise.
  7. Maintain a Flexible Architecture: Design systems with modularity and scalability in mind, allowing easier adjustments as requirements evolve.
  8. Clear Documentation: Ensure comprehensive and up-to-date documentation so that new team members can quickly get up to speed and existing members can easily reference past decisions.
  9. Cross-Training Team Members: Promote knowledge sharing and cross-training within the team to prevent project delays if someone leaves or is unavailable.

Embrace the SOME of the Chaos

Software development is messy, unpredictable, and often maddening. But by recognizing the difference between known unknowns and unknown unknowns, and embracing methodologies that allow for flexibility, we can navigate the chaos more effectively. Next time a deadline whooshes by, remember: it’s not (just) about poor planning. It’s about the nature of the beast itself.

In the end, the key to handling software project deadlines is accepting that some things will always be out of our control. So, let’s embrace SOME of the chaos, adapt on the fly, and maybe, just maybe, we’ll get a bit closer to hitting that elusive target. And if not, there’s always more tea, whiskey and a good sense of humor to see us through. Although that will never make your boss our your client happy.

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I help companies turn their technical ideas into reality. CEO @Sourcetoad and @OnDeck. Author of Herding Cats and Coders. Fan of squash, whiskey, aggressive inline, and temperamental British sports cars.

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Don’t Fall Into the Trap: Why Startup Software Development Isn’t Like Corporate Development

In Startups, Technology

So, you’ve left the corporate world, and now it’s time to build your own startup. You’ve probably managed dev teams before, overseen product launches, maybe even helmed some fancy project management tools that made everything run like a well-oiled machine. You’ve done this before, right? Not exactly. When it’s your startup, everything changes—and, as I’ll explain, if you assume it’ll work the same way, you’re heading for a few surprises.

Startup founders often fall into a dangerous trap when starting a software project from scratch: thinking it’ll be just like building software inside an established company. Here’s why it’s not—and some advice on how to navigate the differences.

1. Switching from Product Manager to Teacher

In an established company, a software team already has two things that give them a serious edge: an existing market and a deep understanding of the business. They’re working within a proven model. Developers in that environment know what questions to ask, can fill in gaps intuitively, and likely understand why they’re building what they’re building.

At a startup, however, your devs are going to need a whole lot more context. They’re not working with familiar requirements—they’re working with your vision, which may be abstract at this stage. If your development team doesn’t understand why something matters, it’s a recipe for ambiguity and frustration on both sides.

Advice: Think of yourself less as a product manager and more as a teacher. Your job is to make sure they understand the core problems, not just the features. Teach them why each requirement matters, help them visualize the end-user, and create that shared language for decision-making. It might feel tedious, but it’s essential to avoid future misalignment and expensive rewrites.

2. Beware of Perfectionism — It’s the Budget Killer

In a large company, products with an existing user base often have to be polished. Features need to be rock-solid, invoices have to be perfect, and everything needs an audit trail. Startups, however, have a different goal: get an MVP in the hands of users fast. It’s a classic trap for first-time founders—focusing on “perfection” and “polish” before knowing if the business model even works.

Startup perfectionism is budget poison. It’s shocking how quickly adding “nice-to-have” features can chew through funding, especially if you’re paying a dev team to build things like automated invoicing or churn management before you’ve even proven people want what you’re selling.

Advice: Ruthlessly strip down your MVP. If a feature doesn’t help you validate your market, it goes on the “later” list. Keep the scope laser-focused on what helps you test your business assumptions. Let the non-essential features wait until you know you have customers who’ll use them.

3. Zen and the Art of the Startup Pivot

Building software for a startup means embracing one cold, hard truth: the business model will change. According to research, 93% of successful startups pivot at least once (and often more). Imagine being asked to go out and passionately sell something that you know might not look the same next year—or next month. It takes a level of zen acceptance that your original idea will likely morph, but that’s what keeps you flexible and ready to capture new opportunities.

For founders, that requires a mindset shift. You have to believe in your product, while also knowing you might be building the “wrong thing” in some way. The focus should be on preserving capital and brainpower for what’s next. The game is less about proving you’re right and more about staying adaptable.

Advice: Budget with pivots in mind. Set your burn rate assuming you’ll need to make big changes. Don’t let ego get in the way of listening to the market, and keep enough gas in the tank for at least one big strategic turn.

4. The Hard Work of Being Your Own “Internal Customer”

Here’s another big one. In a corporate environment, you have internal customers—departments or stakeholders with specific goals that align with the overall company mission. For a startup, the only customer you have is you. You don’t have a preexisting feedback loop from various departments, and you don’t have established success metrics. You have to create that from scratch.

Advice: Start by building an internal customer profile based on your target market, then use that to set clear goals and success criteria for your dev team. If you’re focused on, say, usability for early adopters, set KPIs around usability testing and build from there. By acting as your own “internal customer,” you’re setting a clear direction and saving your team from working in a vacuum.

5. Get Ready to Build AND Sell

Corporate software development often has the luxury of a separate, dedicated sales team to deliver the product to the right audience. As a startup founder, you’re both the builder and the seller. That means you’re not just iterating on software—you’re iterating on messaging, product-market fit, pricing, and maybe even distribution models.

Advice: Factor in time for sales-ready iteration in your dev cycle. As you build, keep track of how each release or update affects the user experience. Ask yourself if the changes make your pitch clearer or simpler and how they align with the current market’s needs. Ultimately, this approach will help you bridge the gap between building the product and ensuring it’s market-ready.

Conclusion

Building software as a startup founder requires a whole different toolkit than you may be used to. You’re part-teacher, part-salesperson, part-zen master, and always the chief budget officer. By recognizing the unique mindset shifts and traps of startup software development, you’re positioning yourself—and your team—for the best chance of success. Focus on creating clarity for your team, set ruthless priorities, embrace change, and never lose sight of the fact that the first version is just the beginning. In the startup world, adaptability isn’t just a skill—it’s the entire game.